Untargeted Metabolomics Yields Insights Into the Lipidome of Botrylloides niger Herdman, 1886, An Ascidian Invading the Mediterranean Sea

Sala, Gerardo Della; Coppola, Daniela; Virgili, Riccardo; Vitale, Giovanni Andrea; Tanduo, Valentina; Teta, Roberta; Crocetta, Fabio; Pascale, Donatella de

doi:10.3389/fmars.2022.865751

Cited by 6 publications

(4 citation statements)

References 113 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Tentative identification of this class of compounds extends to the annotation of lysophophatidyl ethanol amine (LPE) and lysophosphatidyl choline (LPC) grouped in clusters E and F in negative MN (Figure 2) and clusters C and D in positive MN (Figure S2). Additionally, glycerolipids that were detected in A. crassa extract appeared only in positive MN in cluster E (Figure S2) consistent with their N‐containing structures (Della Sala et al., 2022; Wang et al., 2020; Xu et al., 2011).…”

Section: Resultssupporting

confidence: 70%

Seasonal and taxa impact on edible sea cucumber's metabolome and in relation to its cytotoxicity as analyzed via UHPLC/HR‐MS/MS‐based molecular networking and chemometrics

Farag,

El‐Kammar,

Abdelghany

et al. 2024

Food Frontiers

View full text Add to dashboard Cite

Sea cucumbers, belonging to class Holothuroidea, are marine invertebrates with substantial bioactive compounds. This study provides the first comparative metabolome profiling of Holothuria atra and Actinopyga crassa sea cucumbers in relation to their season of collection to dissect between winter and summer samples, providing several first‐time reported metabolites as well as the effect of metabolome variation on their cytotoxic activity against colon and prostate cancer cell lines. Ultrahigh‐performance liquid chromatography coupled with high‐resolution mass spectrometry and global natural products social molecular networking followed by multivariate data analysis were employed for metabolite profiling and seasonal biomarker assignment for each species. The cytotoxic activity was evaluated using in vitro assays against prostate and colon cancer cell lines. A total of 113 metabolites were annotated in both species, including 4 organic acids, 21 sulfoquinovosyl glycerol (sulfolipids), 5 alkyl sulfates, 13 sulfated/saponins, 8 sulfated/triterpene mono/di‐glycosides, 10 triterpenes, 13 sulfated/sterols, 32 phospholipids, 4 sphingolipids, and 3 glycerolipids, several of which are new or first‐time reported. Multivariate data analyses revealed lipid accumulation in summer samples versus triterpene and saponin enrichment in winter‐collected samples, particularly in H. atra, rationalizing its potent cytotoxic activity (IC50 6–12 µg/mL) as revealed using a regression model. However, winter‐collected samples of A. crassa are relatively the least abundant in antinutrient saponins, thus considered to have higher food value.

show abstract

Section: Resultssupporting

confidence: 70%

Seasonal and taxa impact on edible sea cucumber's metabolome and in relation to its cytotoxicity as analyzed via UHPLC/HR‐MS/MS‐based molecular networking and chemometrics

Farag,

El‐Kammar,

Abdelghany

et al. 2024

Food Frontiers

View full text Add to dashboard Cite

show abstract

“…The molecular composition of the SPE fractions was investigated by untargeted Ultra Performance Liquid Chromatography (UPLC) coupled to High Resolution Mass Spectrometry (HRMS) Data Dependent Analysis (DDA), and molecular networking, in an attempt to holistically examine WUR7's metabolome. As previously reported ( 20 ), SPE fractions were employed for untargeted fragmentation data acquisition in order to decrease compound coelution during UHPLC separation and reduce coalescence events, thus improving quality/purity of product ion scans, for a more comprehensive overview of WUR7's metabolome.…”

Section: Resultsmentioning

confidence: 99%

A metabologenomics approach to unlock the metabolome of the novel Antarctic deep-sea isolate Lacinutrix shetlandiensis sp. nov. WUR7

et al. 2023

Self Cite

View full text Add to dashboard Cite

The South Shetland Trough, Antarctica, is an underexplored region for microbiological and biotechnological exploitation. Herein, we describe the isolation and characterisation of the novel bacterium Lacinutrix shetlandiensis sp. nov. WUR7 from a deep-sea environment. We explored its chemical diversity via a metabologenomics approach, wherein the OSMAC strategy was strategically employed to upregulate cryptic genes for secondary metabolite production. Based on hybrid de novo whole genome sequencing and digital DNA–DNA hybridisation, isolate WUR7 was identified as a novel species from the Gram-negative genus Lacinutrix. Its genome was mined for the presence of biosynthetic gene clusters with limited results. However, extensive investigation of its metabolism uncovered an unusual tryptophan decarboxylase with high sequence homology and conserved structure of the active site as compared to ZP_02040762, a highly specific tryptophan decarboxylase from Ruminococcus gnavus. Therefore, WUR7’s metabolism was directed towards indole-based alkaloid biosynthesis by feeding it with L-tryptophan. As expected, its metabolome profile changed dramatically, by triggering the extracellular accumulation of a massive array of metabolites unexpressed in the absence of tryptophan. Untargeted LC-MS/MS coupled with molecular networking, followed along with chemoinformatic dereplication, allowed for the annotation of 10 indole alkaloids, belonging to β-carboline, bisindole, and mono-indole classes, alongside several unknown alkaloids. These findings guided us to the isolation of a new natural bisindole alkaloid 8,9-dihydrocoscinamide B (1), as the first alkaloid from the genus Lacinutrix, whose structure was elucidated on the basis of extensive 1D and 2D NMR and HR-ESIMS experiments. This comprehensive strategy allowed us to unlock the previously unexploited metabolome of Lacinutrix shetlandiensis sp. nov. WUR7.

show abstract

“…The F2 fraction was resuspended in methanol (1 mg/mL) and analyzed through Liquid Chromatography–High-Resolution Tandem Mass Spectrometry (LC HRMS/MS). Experiments were performed using a Thermo LTQ Orbitrap XL high-resolution ESI mass spectrometer coupled to a Thermo U3000 HPLC system (Thermo Fisher Scientific, Waltham, MA, USA) and equipped with a 5-µm C18 column (50 × 2.10 mm, Kinetex) (Phenomenex, Torrance, CA, USA), as already described [ 33 ]. The column was eluted at 200 µL × min −1 with a gradient of 0.1% HCOOH supplemented with H 2 O (solvent A) and CH 3 CN (solvent B).…”

Section: Methodsmentioning

confidence: 99%

New Imidazolium Alkaloids with Broad Spectrum of Action from the Marine Bacterium Shewanella aquimarina

Giugliano,

Della Sala,

Buonocore

et al. 2023

Pharmaceutics

Self Cite

View full text Add to dashboard Cite

The continuous outbreak of drug-resistant bacterial and viral infections imposes the need to search for new drug candidates. Natural products from marine bacteria still inspire the design of pharmaceuticals. Indeed, marine bacteria have unique metabolic flexibility to inhabit each ecological niche, thus expanding their biosynthetic ability to assemble unprecedented molecules. The One-Strain-Many-Compounds approach and tandem mass spectrometry allowed the discovery of a Shewanella aquimarina strain as a source of novel imidazolium alkaloids via molecular networking. The alkaloid mixture was shown to exert bioactivities such as: (a) antibacterial activity against antibiotic-resistant Staphylococcus aureus clinical isolates at 100 µg/mL, (b) synergistic effects with tigecycline and linezolid, (c) restoration of MRSA sensitivity to fosfomycin, and (d) interference with the biofilm formation of S. aureus 6538 and MRSA. Moreover, the mixture showed antiviral activity against viruses with and without envelopes. Indeed, it inhibited the entry of coronavirus HcoV-229E and herpes simplex viruses into human cells and inactivated poliovirus PV-1 in post-infection assay at 200 µg/mL. Finally, at the same concentration, the fraction showed anthelminthic activity against Caenorhabditis elegans, causing 99% mortality after 48 h. The broad-spectrum activities of these compounds are partially due to their biosurfactant behavior and make them promising candidates for breaking down drug-resistant infectious diseases.

show abstract

Untargeted Metabolomics Yields Insights Into the Lipidome of Botrylloides niger Herdman, 1886, An Ascidian Invading the Mediterranean Sea

Cited by 6 publications

References 113 publications

Seasonal and taxa impact on edible sea cucumber's metabolome and in relation to its cytotoxicity as analyzed via UHPLC/HR‐MS/MS‐based molecular networking and chemometrics

Seasonal and taxa impact on edible sea cucumber's metabolome and in relation to its cytotoxicity as analyzed via UHPLC/HR‐MS/MS‐based molecular networking and chemometrics

A metabologenomics approach to unlock the metabolome of the novel Antarctic deep-sea isolate Lacinutrix shetlandiensis sp. nov. WUR7

New Imidazolium Alkaloids with Broad Spectrum of Action from the Marine Bacterium Shewanella aquimarina

Contact Info

Product

Resources

About